Cationic iridium-catalyzed enantioselective activation of secondary sp 3 C-H bond adjacent to nitrogen atom

Shiguang Pan, Yusuke Matsuo, Kohei Endo, Takanori Shibata

Research output: Contribution to journalArticle

63 Citations (Scopus)

Abstract

A cationic Ir(I)-tolBINAP complex catalyzed an enantioselective C-C bond formation, which was initiated by secondary sp 3 C-H bond cleavage adjacent to nitrogen atom. A wide variety of 2-(alkylamino)pyridines and alkenes were selectively transformed into the corresponding chiral amines with moderate to almost perfect enantiomeric excesses. Alkynes were also investigated as coupling partners. The effect of alkyl structure in substrates and directing groups were studied. This transformation represents the first example of a highly enantioselective C-H bond activation of a methylene group, not at allylic or benzylic position.

Original languageEnglish
Pages (from-to)9009-9015
Number of pages7
JournalTetrahedron
Volume68
Issue number44
DOIs
Publication statusPublished - 2012 Nov 4

Keywords

  • C-H activation
  • Enantioselective
  • Heterocycle
  • Iridium

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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